US3989717A - Indolobenzazepine derivatives - Google Patents
Indolobenzazepine derivatives Download PDFInfo
- Publication number
- US3989717A US3989717A US05/559,118 US55911875A US3989717A US 3989717 A US3989717 A US 3989717A US 55911875 A US55911875 A US 55911875A US 3989717 A US3989717 A US 3989717A
- Authority
- US
- United States
- Prior art keywords
- formula
- benzazepine
- methyl
- acid
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- JYGUARFTLQSWDG-UHFFFAOYSA-N 3,12-diazatetracyclo[9.7.0.02,8.013,18]octadeca-1,3,5,7,9,11,13,15,17-nonaene Chemical class C1=CC=NC2=C3C4=CC=CC=C4N=C3C=CC2=C1 JYGUARFTLQSWDG-UHFFFAOYSA-N 0.000 title abstract description 8
- 239000002253 acid Chemical group 0.000 claims abstract description 23
- 150000003839 salts Chemical class 0.000 claims abstract description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 12
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- CRUKEDNIFQWKEO-KDOFPFPSSA-N trans-1,2,6,7-tetrahydro-2-methyl-1-(2-methylaminoethyl)-indolo[1,7-ab][1]benzazepine Chemical compound C1CC2=CC=CC=C2N2[C@@H](CCNC)[C@H](C)C3=CC=CC1=C32 CRUKEDNIFQWKEO-KDOFPFPSSA-N 0.000 claims description 6
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- 235000012222 talc Nutrition 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- RMSQXAKIXRMWIT-BEFAXECRSA-N trans-1-(2-ethylaminoethyl)-1,2,6,7-tetrahydro-2-methylindolo[1,7-ab][1]benzazepine Chemical compound C1CC2=CC=CC=C2N2[C@@H](CCNCC)[C@H](C)C3=CC=CC1=C32 RMSQXAKIXRMWIT-BEFAXECRSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/06—Peri-condensed systems
Definitions
- R 3 and R 4 both represent a methyl group or both represent an ethyl group or R 3 represents a methyl or ethyl group and R 4 represents a benzyl group,
- R 3 and R 4 have the significance given earlier.
- This syrup was a mixture of 1-(2-dimethylaminoethyl)-6,7-dihydro-2-methylindolo[1,7-ab]-[1]benzazepine and 1-(2-dimethylaminoethyl)-1,2,6,7-tetrahydro-2-methylene-indolo[1,7-ab] [1]benzazepine.
- the basic product was distilled at ca 150° C (air-bath temperature)/10 - 5 mm Hg to give the trans-1,2,6,7-tetrahydro-2-methyl-1-(2-methylaminoethyl)-indolo[1,7-ab][1]benzazepine whose hydrochloride melted at 198°-200° C.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1320774A GB1464431A (en) | 1974-03-25 | 1974-03-25 | Indolobenzazepine derivatives and a process for the manufacture thereof |
| UK13207/74 | 1974-03-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3989717A true US3989717A (en) | 1976-11-02 |
Family
ID=10018788
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US05/559,118 Expired - Lifetime US3989717A (en) | 1974-03-25 | 1975-03-17 | Indolobenzazepine derivatives |
Country Status (25)
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4171443A (en) * | 1978-05-08 | 1979-10-16 | Ayerst, Mckenna & Harrison Limited | 10B-Azafluoranthene derivatives and precursors thereof |
| US4217454A (en) * | 1976-04-15 | 1980-08-12 | Endo Laboratories, Inc. | Process for stereoselectively reducing indole derivatives |
| US4965259A (en) * | 1987-12-31 | 1990-10-23 | Egis Gyogyszergyar | Dioxazocine derivatives compositions and methods containing them having antidepressive, spasmolytic, anticonvulsive, and antiarrhythmic properties |
| US5173489A (en) * | 1986-04-10 | 1992-12-22 | The Dupont Merck Pharmaceutical Co. | α,α-disubstituted aromatics and heteroaromatics as cognition enhancers |
| USD669373S1 (en) * | 2010-06-23 | 2012-10-23 | Institut de Radioprotection et de Nucleaire | Ring of dosimetry |
-
1974
- 1974-03-25 GB GB1320774A patent/GB1464431A/en not_active Expired
-
1975
- 1975-01-01 AR AR258001A patent/AR206624A1/es active
- 1975-02-28 CH CH256075A patent/CH609696A5/xx not_active IP Right Cessation
- 1975-02-28 CH CH1098178A patent/CH612196A5/xx not_active IP Right Cessation
- 1975-03-10 ZA ZA00751460A patent/ZA751460B/xx unknown
- 1975-03-13 IL IL46823A patent/IL46823A/xx unknown
- 1975-03-17 US US05/559,118 patent/US3989717A/en not_active Expired - Lifetime
- 1975-03-19 PH PH16929A patent/PH11630A/en unknown
- 1975-03-19 NL NL7503268A patent/NL7503268A/xx not_active Application Discontinuation
- 1975-03-21 FR FR7508904A patent/FR2265395B1/fr not_active Expired
- 1975-03-21 HU HUHO1781A patent/HU169332B/hu unknown
- 1975-03-21 SE SE7503302A patent/SE7503302L/xx unknown
- 1975-03-24 ES ES435969A patent/ES435969A1/es not_active Expired
- 1975-03-24 NO NO751009A patent/NO751009L/no unknown
- 1975-03-24 AT AT224875A patent/AT342599B/de not_active IP Right Cessation
- 1975-03-24 DK DK123575AA patent/DK138993B/da unknown
- 1975-03-24 JP JP50034593A patent/JPS50130796A/ja active Pending
- 1975-03-24 SU SU7502116189A patent/SU576930A3/ru active
- 1975-03-24 DD DD184979A patent/DD118632A5/xx unknown
- 1975-03-24 PL PL1975179032A patent/PL94151B1/pl unknown
- 1975-03-24 BR BR1757/75A patent/BR7501757A/pt unknown
- 1975-03-24 BE BE154636A patent/BE827048A/xx unknown
- 1975-03-24 LU LU72119A patent/LU72119A1/xx unknown
- 1975-03-24 PL PL1975191589A patent/PL97903B1/pl unknown
- 1975-03-25 FI FI750897A patent/FI750897A/fi not_active Application Discontinuation
- 1975-03-25 DE DE19752513197 patent/DE2513197A1/de active Pending
- 1975-04-25 CU CU34238A patent/CU34238A/es unknown
-
1976
- 1976-01-30 SU SU7602317504A patent/SU576929A3/ru active
- 1976-02-13 ES ES445144A patent/ES445144A1/es not_active Expired
- 1976-09-06 PH PH18868A patent/PH11763A/en unknown
- 1976-09-06 PH PH18867A patent/PH11758A/en unknown
Non-Patent Citations (2)
| Title |
|---|
| Chem. Abs. vol. 60: 2916, (1963) abs. of Brit. Pat. 936,783. * |
| wagner et al., Synthetic Organic Chemistry (1953) pp. 7,675-7,676. * |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4217454A (en) * | 1976-04-15 | 1980-08-12 | Endo Laboratories, Inc. | Process for stereoselectively reducing indole derivatives |
| US4171443A (en) * | 1978-05-08 | 1979-10-16 | Ayerst, Mckenna & Harrison Limited | 10B-Azafluoranthene derivatives and precursors thereof |
| US5173489A (en) * | 1986-04-10 | 1992-12-22 | The Dupont Merck Pharmaceutical Co. | α,α-disubstituted aromatics and heteroaromatics as cognition enhancers |
| US4965259A (en) * | 1987-12-31 | 1990-10-23 | Egis Gyogyszergyar | Dioxazocine derivatives compositions and methods containing them having antidepressive, spasmolytic, anticonvulsive, and antiarrhythmic properties |
| USD669373S1 (en) * | 2010-06-23 | 2012-10-23 | Institut de Radioprotection et de Nucleaire | Ring of dosimetry |
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